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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Recommended by 100% of travelers
Chicago, USA
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

Why travelers loved this

5.0
·
· HeidiHairston ·
Jul 2025
Amazing time with Captain Ulysses! It was a beautiful day with great company and a great host! The views were incredible and the conversation fun! We had music and drinks and it was a lovely day on the lake!
· Jeffrey_F ·
Jul 2025
We 5 ladies enjoyed a beautiful afternoon sailing! The boat was clean and comfortable. Captain Mike was knowledgeable and friendly. The afternoon was perfect!

Overview

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.
  • Itineraries are fully customizable to your group’s interests
  • Use a Bluetooth-enabled device to get your tunes playing
  • See a view of Chicago that few other visitors get to admire
  • Choose from several start times to best suit your schedule

What's Included

  • Professional US Coast Guard licensed captain
  • Use of Bluetooth speakers
  • All taxes
  • Navy Pier Facility Fee
  • Gratuities
  • Food and Drinks
  • Parking

Meeting and Pickup

Meeting point

  • 801 E Grand Ave, Chicago, IL 60611, USA

    We operate from the new Navy Pier Marina located along the north side of Navy Pier. Please gather outside of Navy Pier Marina - Gate D and then text/call us to tell us that you are here. We will welcome you to the marina and escort you to the sailboat.

End point

This activity ends back at the meeting point.

Itinerary

1

Come Sailing, Inc.

2 hours Admission Ticket Included

Navy Pier (Pass By)

Chicago Skyline (Pass By)

Adler Planetarium (Pass By)

Soldier Field (Pass By)

Clarence F. Buckingham Fountain (Pass By)

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Near public transportation
  • Most travelers can participate
  • NO SMOKING - All charters are NON-SMOKING. Use of any tobacco products, cigars, pipes, cigarettes, e-cigarettes, vapor devices, etc. are strictly prohibited. Use of any of these products may result in a non-refundable, early termination of your charter and the assessment of a cleaning fee.
  • CONSUMPTION OF ALCOHOL - Customers and guests may bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
  • NO GLASS ON BOARD - Glass containers are prohibited. Please do not bring them. Wine and Champagne bottle are permitted as long as they remain secure in a protective container during charter. Please bring plastic cups for drinking.
  • CUSTOMER/GUEST BEHAVIOR - Customers and guests are expected to conduct themselves in an appropriate manner. Inappropriate behavior will not be tolerated. Any behavior determined by the captain to be inappropriate (lewd, offensive, unsafe, etc.) may result in a non-refundable, early termination of your charter.
  • WEAPONS ARE STRICTLY PROHIBITED - Weapons on any kind are strictly prohibited! Guns, knives, or weapons of any kind are NOT allowed on board our vessels at any time. Bringing any of these prohibited items aboard may result in a non-refundable, early termination of your charter.
  • ANIMALS ARE PROHIBITED - Unfortunately, we cannot accommodate animals of any type.
  • SWIMMING MAY BE PERMITTED - Swimming may be permitted on charters of 3 hours or longer. Swimming is not guaranteed and is at the captain's discretion. If swimming is deemed permissible by the captain, every passenger on board will be required to sign a waiver & release prior to swimming. Swimming will not be allowed after the departure time of our Sunset Sail scheduled for that same day. SWIMMING IS AT YOUR OWN RISK!
  • FOOD AND BEVERAGE - Food and beverages may be consumed on deck. Please clean up any spilled food or beverage and take your garbage with you. A cleaning fee may be assessed for excessive spillage.
  • SEASICKNESS/MOTION SICKNESS - Any person that experiences seasickness must remain on deck. The cabin area below deck is NOT an appropriate place for any person to deal with seasickness. A cleaning fee will be assessed for any person vomiting anywhere in the below deck cabin area of the sailboat, including the “head”/bathroom.
  • GALLEY STOVE AND SINK - The galley stove onboard our sailboat is NOT for use by customers. The sinks on board our boats drain directly into the lake and are NOT intended for food prep nor for disposing of unwanted items. None of the sinks have garbage disposals. Please do NOT treat our sinks like you treat your kitchen sink. They are NOT the same.
  • CLEANING FEES - Cleaning fees, if applicable, will be equivalent to the standard, full price of your charter.
  • TERMINATION OF CHARTER - The captain reserves the right to cancel a charter at any time for reasons of weather, mechanical failure, or safety. Charters will be rescheduled at the customer’s convenience. A refund will be offered if rescheduling cannot be agreed upon.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • BOOKING ERRORS - We reserve the right to cancel reservations that are the result of incorrect pricing/availability due to malicious acts or software/website errors.
  • CONSENT TO BE FILMED/PHOTOGRAPHED - Boarding our sailboats is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting our company, its agents, successors, assignees and affiliates, and their respective employees, officers, directors, shareholders, and representatives the right and permission to use such film, photographs, and recordings of your voice, image, and likeness for the purpose of promoting our company and its related services. You further agree that you will not receive any financial compensation or cash payment for the rights or permissions granted by you. In such case that you are the parent or guardian of any minor child that has accompanied you aboard our sailboat, you further consent to the foregoing on behalf of that minor child.
  • This is a private tour/activity. Only your group will participate

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)
Gallery picture 2 (from a traveler's review)
Gallery picture 3 (from a traveler's review)
Gallery picture 4 (from a traveler's review)
Gallery picture 5 (from a traveler's review)

Featured review

Kira_M
We took a two hour sail for our daughter’s 24th birthday. It was fantastic! Everyone in the family felt like it was the best part of our vacation. Captain Mike was awesome and answered all kinds of questions about sailing and some Chicago history. I cannot recommend this enough!

Reviews

5.0
based on 70 reviews
Total reviews and rating from Viator & Tripadvisor

Fantastic voyage

Polly_M, Sep 2025
Wonderful way to experience the Chicago skyline Captain Mike was awesome, time flew by and we want to do it again.

A great time out on the...

Stephen_M, Aug 2025
A great time out on the lake. Our captain was very capable and informative. I would recommend for just a fun experience or for a special occasion.

Best way to experience Lake Michigan

Michelle_T, Aug 2025
Great experience. I would have been on there all day if I could! It was a wonderful way and intimate experience to be on Lake Michigan in a sailboat and not with a lot of other people.

A beautiful day on the lake!

Jeffrey_F, Jul 2025
We 5 ladies enjoyed a beautiful afternoon sailing! The boat was clean and comfortable. Captain Mike was knowledgeable and friendly. The afternoon was perfect!

Best Part of Our Trip

Kira_M, Jul 2025
We took a two hour sail for our daughter’s 24th birthday. It was fantastic! Everyone in the family felt like it was the best part of our vacation. Captain Mike was awesome and answered all kinds of questions about sailing and some Chicago history. I cannot recommend this enough!

Sail with Captain Ulysses!

HeidiHairston, Jul 2025
Amazing time with Captain Ulysses! It was a beautiful day with great company and a great host! The views were incredible and the conversation fun! We had music and drinks and it was a lovely day on the lake!

Highly recommend

Marisa_S, Sep 2024
Mike was awesome! A beautiful experience on Lake Michigan! Thank you for being a great captain! Would definitely do again.

Great tour, super communication!

Melissa_W, Aug 2024
Charter Captain was wonderful. Very patient and sensitive to our needs as we were there to put my dad’s ashes in Lake MI. Highly recommend Cpt Michael for any special occasion trip or just a lovely regular sail.

Come Sailing!

Mari, Aug 2024
Lovely morning sail on Lake Michigan with the skillful, personable and knowledgeable Captain Ulysses!

Perfect Trip!

Anita_H, Aug 2024
It was a perfect trip up and down the shore with spectacular downtown views. Captain Mike was great, a perfect treat for friends to share on a warm summer day!

Private charter

Angelia_N, Aug 2024
We drove up to Chicago from Indianapolis to celebrate my husband’s 60th birthday. I wanted to find something different and fun to do. I came across this private charter and booked it. The weather was beautiful, we had such a wonderful time out on the water with Captain Mike! If you’re looking for a fun and relaxing time on the water I would highly recommend booking this excursion!

Beautiful Day on the Sail Boat

Megan_F, Sep 2023
The views were amazing. The Captain was very nice and professional. Such a relaxing way to spend the day

Anniversary Ride

DeWayne_P, Aug 2023
Great experience as part of our 19th anniversary celebration. Beautiful views and great captain and service. Bluetooh music was a nice touch.

My favorite Chicago excursion!

Leslie_M, Jul 2023
The sail boat was beautiful and very clean. Captain Ulysses was a great guide and captain. We loved the views of the city from the lake. It was my favorite outing of our trip to Chicago. Our teen kids had a great time too.

Smooth sailing!

Rosie_F, Jul 2023
Rich was the best captain on the waters! He shared so much great history about the lake and Chicago with us and made our ride smooth sailing! Wish we would have booked a much longer ride but we’ll be back!

Family fun on Lake Michigan

Joseph_C, Jun 2023
Wonderful day out on the water! Visited Chicago many times before, but first time out on Lake Michigan. Will be making this a tradition every time I visit during warmer months!

Book it!

Misty_T, Jun 2023
This tour was the highlight of our girls’ weekend. Ulysses was fabulous and the views were gorgeous.

Response from Host, Jun 2023

Thanks for the glowing review Misty! Glad you had a great experience! Capt. Mike

Sailing… it really does take you away….

Maryalida_B, Sep 2022
It was a great chance to kick off the fall with a sailing trip with friends. Captain Mike was a great captain and host - we asked hundreds of questions and learned a little bit about sailing and a whole host of other related topics. The Bernard was perfect for six - and we had plenty of room to spread out - take photos - and just enjoy the afternoon. Looking forward to booking again.

We had a great time sailing with Captain Mike!

Chris_C, Aug 2022
We had an amazing time! Captain Mike took care of everything so we could just relax and enjoy the ride. I would definitely recommend this experience.

Captain Mike was awesome,...

Roberto_P, Aug 2022
Captain Mike was awesome, really friendly, making the trip truly memorable. The city of Chicago is the perfect backdrop, so we absolutely recommend!

Very relaxing and...

Lynn_R, Aug 2022
Very relaxing and enjoyable Did the sailing trip as a family celebrating a birthday Weather was great and captain Mike was very knowledgeable and pleasant to have as a captain

South comes to big city

Keith_M, Jul 2022
Great sailing experience. Very professional captain…on time. Felt extremely safe. Beautiful way to view the city

Great

Alyssa_R, Jul 2022
Captain Mike was amazing! Made us comfortable and was educated on sailing. Will definitely be sailing with him again!

Response from Host, Jul 2022

Thanks Alyssa! I look forward to sailing with you again! Capt. Mike

Captain was great!...

Megan_D, Jul 2022
Captain was great! Sailing was great! We had a blast! Would highly recommend this to anyone who enjoys being out on the water.

Perfect teen activity

Allyson_P, Jul 2022
This was by far an amazing, relaxing and great family activity. Our teenagers loved it. Views were stunning, captains were super laid back and kind. They just wanted us to enjoy ourselves you could tell. Would definitely recommend this to anyone looking for a fun date idea, teen kid idea or even solo. It’s so peaceful out on the water with no engine noise just the water and the sails.

Williams Sailing Experience

Sally_W, Jul 2022
Captain Mike was excellent, knowledge is A1 we had a great time throughly enjoyed Would Highly recommend

Sailing out on the lake...

Keadren_G, Jun 2022
Sailing out on the lake was wonderful. Captain Mike is the absolute best….we had a great family time. Would recommend very highly.

Response from Host, Jun 2022

Thanks Keadren! I'm so glad to hear how much you enjoyed your time on Lake Michigan! Please come sail with us again next time you're in town.

Nuvision marketing group

Blair_H, Jun 2022
Captain Mike was fantastic two years in a row. Weather was perfect as well as time spent with family. This will be annual event going forward.

Response from Host, Jun 2022

We love it when customers come back to sail with us again! Thanks Blair! We appreciate your business! Always a pleasure! Capt. Mike

Family fun

Tania_G, Jun 2022
After all the walking and sightseeing this is a great way to relax and enjoy the Chicago skyline. It was a pleasure sailing with Captain Mike. We would definitely do this again.

Response from Host, Jun 2022

Thank you Tania!

Excellent experience....

Robert_G, Jun 2022
Excellent experience. Captain Mike provided the perfect afternoon sailing that created memories for a lifetime Only recommendation would to use GPS coordinates for the pick up site. That way easier to copy and paste into a map application. Thank you

Response from Host, Jun 2022

It's always rewarding to hear when people have such great experiences! Thanks for sailing with us Robert!
Likely to Sell Out

From $507.96

per group (up to 6)

up to 24 hours before the experience starts (local time)

Book ahead!
On average, this is booked 24 days in advance.

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